Abstract
The Mannich-like reactions of the enolates generated from 2,3-di-O-protected 6-deoxy-4-O-propionyl-α-D-glucopyranosides with (3R,4R)-4-acetoxy-3-1(R)-1 -(t-buiyldimethylsilyloxy)ethyl ]azetidin-2-one were investigated. The corresponding 2,3-di-O-methyl derivative provided the Mannich adduct in good to excellent stereoselectivity. From the major adduct, the azetidin-2-one incorporating an α-methyl acetic acid side chain at the Opposition with β-configuration was obtained by alkaline hydrolysis. This product, (35,45)-3-[(R)-1 (t-butyldimethylsilyloxy)ethyl [-4-](R)-1 -carboxyethyl |azetidin-2-one, is a useful intermediate for the 1 β-methylcarbapenem synthesis.
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